DE2517784A1 - Neue crotonamide, verfahren zu deren herstellung und herbizide zusammensetzungen - Google Patents
Neue crotonamide, verfahren zu deren herstellung und herbizide zusammensetzungenInfo
- Publication number
- DE2517784A1 DE2517784A1 DE19752517784 DE2517784A DE2517784A1 DE 2517784 A1 DE2517784 A1 DE 2517784A1 DE 19752517784 DE19752517784 DE 19752517784 DE 2517784 A DE2517784 A DE 2517784A DE 2517784 A1 DE2517784 A1 DE 2517784A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxycrotonamide
- acetylacetamide
- crotonamides
- hours
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims description 44
- 230000002363 herbicidal effect Effects 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 4
- -1 1 -cyclohexenyl Chemical group 0.000 claims description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000011149 active material Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003869 acetamides Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 24
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 23
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 238000004821 distillation Methods 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 240000006162 Chenopodium quinoa Species 0.000 description 12
- 241000219793 Trifolium Species 0.000 description 11
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 11
- 241001184547 Agrostis capillaris Species 0.000 description 10
- 235000015493 Chenopodium quinoa Nutrition 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- 244000098338 Triticum aestivum Species 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 241000743985 Alopecurus Species 0.000 description 9
- 241000723353 Chrysanthemum Species 0.000 description 9
- 235000007516 Chrysanthemum Nutrition 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 8
- 240000005702 Galium aparine Species 0.000 description 7
- 235000014820 Galium aparine Nutrition 0.000 description 7
- 240000004296 Lolium perenne Species 0.000 description 7
- 244000075850 Avena orientalis Species 0.000 description 6
- 235000021501 Rumex crispus Nutrition 0.000 description 6
- 244000207667 Rumex vesicarius Species 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000007319 Avena orientalis Nutrition 0.000 description 5
- 235000021533 Beta vulgaris Nutrition 0.000 description 5
- 241000335053 Beta vulgaris Species 0.000 description 5
- 241000209219 Hordeum Species 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- UJRCLZKWBWUTRC-UHFFFAOYSA-N 2-ethoxy-3-methylbutane Chemical compound CCOC(C)C(C)C UJRCLZKWBWUTRC-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- XEDYFFMSZLFWLT-UHFFFAOYSA-N n-(1-adamantyl)-3-oxobutanamide Chemical compound C1C(C2)CC3CC2CC1(NC(=O)CC(=O)C)C3 XEDYFFMSZLFWLT-UHFFFAOYSA-N 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 241000743339 Agrostis Species 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000723352 Leucanthemum maximum Species 0.000 description 2
- 241001162899 Poa alopecurus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WISHOQVCIWQGMO-UHFFFAOYSA-N n-cyclooctyl-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1CCCCCCC1 WISHOQVCIWQGMO-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- QSBDRCYMAZSHPD-ARJAWSKDSA-N (Z)-3-methoxybut-2-enamide Chemical compound CO\C(=C/C(=O)N)\C QSBDRCYMAZSHPD-ARJAWSKDSA-N 0.000 description 1
- CUOUTCMJTVMQGJ-NTMALXAHSA-N (z)-3-methoxy-n-(4-methylcyclohexyl)but-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1CCC(C)CC1 CUOUTCMJTVMQGJ-NTMALXAHSA-N 0.000 description 1
- ACUDEWRQGQRIKH-HJWRWDBZSA-N (z)-n-cyclohex-3-en-1-yl-3-methoxybut-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1CCC=CC1 ACUDEWRQGQRIKH-HJWRWDBZSA-N 0.000 description 1
- SWIGTDMQBVFMHQ-KHPPLWFESA-N (z)-n-cyclooctyl-3-methoxybut-2-enamide Chemical compound CO\C(C)=C/C(=O)NC1CCCCCCC1 SWIGTDMQBVFMHQ-KHPPLWFESA-N 0.000 description 1
- YDBHSDRXUCPTQQ-UHFFFAOYSA-N 1-methylcyclohexan-1-amine Chemical compound CC1(N)CCCCC1 YDBHSDRXUCPTQQ-UHFFFAOYSA-N 0.000 description 1
- JYDYHSHPBDZRPU-UHFFFAOYSA-N 3-methylcyclohexan-1-amine Chemical compound CC1CCCC(N)C1 JYDYHSHPBDZRPU-UHFFFAOYSA-N 0.000 description 1
- FIPZFJXPLSDNKG-UHFFFAOYSA-N 3-oxo-n-(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)butanamide Chemical compound C1CC2(C)C(NC(=O)CC(=O)C)CC1C2(C)C FIPZFJXPLSDNKG-UHFFFAOYSA-N 0.000 description 1
- QCPSOHMYNZCMGS-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydro-1h-4,7-methanoinden-6-amine Chemical compound C12CC=CC2C2CC(N)C1C2 QCPSOHMYNZCMGS-UHFFFAOYSA-N 0.000 description 1
- MDFWXZBEVCOVIO-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptan-3-amine Chemical compound C1CC2(C)C(N)CC1C2(C)C MDFWXZBEVCOVIO-UHFFFAOYSA-N 0.000 description 1
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 235000007871 Chrysanthemum coronarium Nutrition 0.000 description 1
- 244000067456 Chrysanthemum coronarium Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001085205 Prenanthella exigua Species 0.000 description 1
- 241000219053 Rumex Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
- NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- BJRAKBBIWKMZIQ-UHFFFAOYSA-N n-(3-methylcyclohexyl)-3-oxobutanamide Chemical compound CC1CCCC(NC(=O)CC(C)=O)C1 BJRAKBBIWKMZIQ-UHFFFAOYSA-N 0.000 description 1
- HJGPVOZTYFYBEH-UHFFFAOYSA-N n-(4-methylcyclohexyl)-3-oxobutanamide Chemical compound CC1CCC(NC(=O)CC(C)=O)CC1 HJGPVOZTYFYBEH-UHFFFAOYSA-N 0.000 description 1
- KQAGKUTVBOPZCI-UHFFFAOYSA-N n-acetyl-2-cyclohexylacetamide Chemical compound CC(=O)NC(=O)CC1CCCCC1 KQAGKUTVBOPZCI-UHFFFAOYSA-N 0.000 description 1
- GXPBEASXDUYTKA-UHFFFAOYSA-N n-cyclohexyl-3,3-dimethoxybutanamide Chemical compound COC(C)(OC)CC(=O)NC1CCCCC1 GXPBEASXDUYTKA-UHFFFAOYSA-N 0.000 description 1
- FLCPERRDPXWFDK-UHFFFAOYSA-N n-cyclohexyl-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1CCCCC1 FLCPERRDPXWFDK-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WIONSVZCWDNLDJ-UHFFFAOYSA-N quinoline;toluene Chemical compound CC1=CC=CC=C1.N1=CC=CC2=CC=CC=C21 WIONSVZCWDNLDJ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7413891A FR2268010B1 (enrdf_load_stackoverflow) | 1974-04-22 | 1974-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2517784A1 true DE2517784A1 (de) | 1975-10-30 |
Family
ID=9137926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752517784 Withdrawn DE2517784A1 (de) | 1974-04-22 | 1975-04-22 | Neue crotonamide, verfahren zu deren herstellung und herbizide zusammensetzungen |
Country Status (17)
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744817A (en) * | 1954-10-13 | 1956-05-08 | Dow Chemical Co | Method and composition for the control of the growth of undesirable vegetation |
| US3278597A (en) * | 1963-05-08 | 1966-10-11 | Gulf Oil Corp | Substituted tiglanilide herbicides |
| US3291592A (en) * | 1964-04-20 | 1966-12-13 | Du Pont | Method for increasing sugar cane yield |
| DE1593405A1 (de) * | 1966-07-29 | 1971-07-22 | Spezialchemie Gmbh & Co | Verfahren zur Darstellung von Alkoxycrotonsaeureestern |
| CH508594A (de) * | 1968-03-25 | 1971-06-15 | Bayer Ag | Verfahren zur Herstellung von B-Alkoxyacryl-säureamiden |
| US3657340A (en) * | 1969-01-31 | 1972-04-18 | Dow Chemical Co | Process for preparing substituted beta-haloacrylamides |
| US3703518A (en) * | 1969-07-28 | 1972-11-21 | Chisso Corp | Method for producing beta-amino-crotonamide |
| JPS5033064B2 (enrdf_load_stackoverflow) * | 1971-10-23 | 1975-10-27 | ||
| FR2201035B1 (enrdf_load_stackoverflow) * | 1972-09-26 | 1980-04-25 | Roussel Uclaf |
-
1974
- 1974-04-22 FR FR7413891A patent/FR2268010B1/fr not_active Expired
-
1975
- 1975-03-31 IL IL46981A patent/IL46981A/xx unknown
- 1975-04-16 US US05/568,383 patent/US4170465A/en not_active Expired - Lifetime
- 1975-04-18 DD DD185546A patent/DD118980A5/xx unknown
- 1975-04-18 HU HU75RO835A patent/HU173270B/hu unknown
- 1975-04-18 ES ES436741A patent/ES436741A1/es not_active Expired
- 1975-04-21 BE BE155603A patent/BE828174A/xx unknown
- 1975-04-21 IT IT49217/75A patent/IT1045541B/it active
- 1975-04-21 CA CA000225091A patent/CA1042427A/fr not_active Expired
- 1975-04-21 LU LU72331A patent/LU72331A1/xx unknown
- 1975-04-21 IE IE898/75A patent/IE41332B1/xx unknown
- 1975-04-21 GB GB1631175A patent/GB1447339A/en not_active Expired
- 1975-04-21 CH CH507775A patent/CH599126A5/xx not_active IP Right Cessation
- 1975-04-22 DE DE19752517784 patent/DE2517784A1/de not_active Withdrawn
- 1975-04-22 JP JP50048256A patent/JPS50148330A/ja active Pending
- 1975-04-22 NL NL7504739A patent/NL7504739A/xx not_active Application Discontinuation
- 1975-04-22 DK DK171975A patent/DK171975A/da active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| NL7504739A (nl) | 1975-10-24 |
| GB1447339A (en) | 1976-08-25 |
| DK171975A (da) | 1975-10-23 |
| CH599126A5 (enrdf_load_stackoverflow) | 1978-05-12 |
| BE828174A (fr) | 1975-10-21 |
| IT1045541B (it) | 1980-05-10 |
| CA1042427A (fr) | 1978-11-14 |
| IL46981A (en) | 1978-04-30 |
| LU72331A1 (enrdf_load_stackoverflow) | 1976-03-17 |
| IL46981A0 (en) | 1975-05-22 |
| FR2268010B1 (enrdf_load_stackoverflow) | 1976-10-29 |
| JPS50148330A (enrdf_load_stackoverflow) | 1975-11-27 |
| US4170465A (en) | 1979-10-09 |
| ES436741A1 (es) | 1977-01-01 |
| DD118980A5 (enrdf_load_stackoverflow) | 1976-04-05 |
| IE41332B1 (en) | 1979-12-05 |
| FR2268010A1 (enrdf_load_stackoverflow) | 1975-11-14 |
| IE41332L (en) | 1975-10-22 |
| HU173270B (hu) | 1979-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |